A Destination Guide To Chicago, Illinois

Cloud Gate - Chicago | www.rtwgirl.com
Planning a trip to Chicago?? Add a couple of these to your itinerary!!! 

I often get asked for recommendations by friends when they travel so I’ve decided to compile and re-write some of my earlier posts into destination guides. Today’s guide is for Chicago!!!

Chicago is a very underrated city. If you have been I am sure you already love it. If you haven’t, I’ll be bold and say that it is my favorite American city. Minus the winter, Chicago is pretty perfect, especially for visitors from other countries.


Why I love Chicago!

  • It’s easy to get around via public transport
  • The food scene is incredible (warning: you may gain 10 pounds on a week visit)
  • If you’re a guy and you’re into sports, it’s a mecca with the Bears, the Bulls, the Cubbies, and the Sox.
  • The architecture is amazing!
  • There are great museums along with great cultural events like festivals, musicals, dance, and theater.
  • And last but not least, Chicagoans are so nice.

People typically visit New York, San Francisco, and Los Angeles when traveling to the US and forget about all about Chicago. I think a lot of foreigners would be pleasantly surprised with this gem of a city.

What To Do

A great thing about Chicago is it’s easy to use its public transportation system. You can take the bus or ride their version of the subway called the L (elevated line) seen below.

Chicago L | www.rtwgirl.com

Taking the L

Millennium Park

Here are some photos from an afternoon at Millennium Park. It’s a public park space along the Lake Michigan shoreline in the Loop area of downtown Chicago. It is a tourist attraction but it’s awesome and a can’t miss part of the city.

Millennium Park Crown Fountain - Chicago | www.rtwgirl.com

Crown Fountain, an interactive public art and video sculpture in Millennium Park

Milliennium Park Crown Fountain - Chicago | www.rtwgirl.com

Crown Fountain’s video changes and features local residents’ images and is also a water park.

Jay Pritzker Pavilion - Chicago | www.rtwgirl.com

For all you architecture fans!! The Jay Pritzker Pavilion by Frank Gehry

Cloud Gate- Chicago | www.rtwgirl.com

Cloud Gate aka the Bean!

Cloud Gate - Chicago | www.rtwgirl.com

Underneath Cloud Gate aka the Bean

Cloud Gate Reflections- Chicago | www.rtwgirl.com

Reflections of the city onto Cloudgate

Chicago Reflections - Chicago | www.rtwgirl.com

My friend Danny and I taking our selfies against Cloud Gate!

Reflections at Cloud Gate - Chicago | www.rtwgirl.com

Up close and personal with Cloud Gate

Must do 

One thing I recommend is the architectural boat tour. I’ve taken it but alas don’t have my old photos. I would totally do it again!

Chicago Architectural Boat Tour | www.rtwgirl.com

Boat touring!

If you don’t take the boat tour, just walk around downtown. It’s very manageable and safe. You’ll see some fantastic architecture like the famous Marina City Towers. People think that they are parking garages because you can see cars parked but it’s a mixed-use building. There are offices, businesses down below, and apartments.

Marina City Towers Chicago | www.rtwgirl.com

Marina City By Bertrand Goldberg. Probably one of my favorite buildings in the world.

Wrigley Building | www.rtwgirl.com

The Wrigley Building

View of Chitown

There’s a load of great views like this one from the Aon Building. (Excuse the old, low res photo)

I’ve yet to take a picture at the Willis Tower aka the Sears Tower (black building seen above). I’ve had lunch there and even gone as a child but I haven’t gone on their Skydeck. Something to do for next time! There’s a lot of art in public spaces in Chicago. One example is this piece by Alexander Calder in front of the Federal Plaza.

Flamingo by Alex Calder - Chicago | www.rtwgirl.com

Flamingo by Alexander Calder

Chicago Destination Guide | www.rtwgirl.com

Gorgeous Chicago at dusk

Sports are a huge thing in Chicago. Even if you’re not into sports it’s fun to catch a game. I’ve yet to catch a Bulls game and I love basketball. I have caught a Chicago Cubs baseball game at Wrigley Field. It’s so fun to eat peanuts, drink beer, and cheer on the team with locals.

Wrigley Field Cubs - Chicago | www.rtwgirl.com

Go Cubbies!!!

If you’re a fan of art there are several of notable museums and galleries in Chicago like the Art Institute below or the Museum of Contemporary Art.

Art Institute of Chicago | www.rtwgirl.com

Can’t-miss the Art Institute which is next to Millennium and Grant Park



Where To Eat

Pot Belly Chicago | www.rtwgirl.com

I’m not all fancy. I love Potbelly’s, which is a Chicago sandwich institution now seen in other cities.

Wow Bao Chicago | www.rtwgirl.com

Mongolian beef bao

Wow Bao dumplings! It’s one of the best budget-friendly snacks around Chicago! I grab a couple of these when I’m shopping at Water Tower Place to tie me over till the next meal.

Wow Bao Chicago | www.rtwgirl.com

Coconut creme filling bao

Italian Beef - Chicago Destination Guide | www.rtwgirl.com

There are some Chicago-specific foods you need to try! One of them is an Italian Beef. Italian Beefs are another Chicago specific dish. It’s a sandwich with roast beef, meat drippings on an Italian roll and topped with giardiniera (pepper mix). It’s sooo good! I’ve had them at Portillo’s but try Al’s Beef.

Garret's Popcorn Chicago | www.rtwgirl.com

Have you ever had Chicago-style popcorn? It’s a mix of caramel and cheese popcorn. Try Garret’s if you like popcorn! Several locations around the city but they this their stand at O’Hare airport.

For budget-friendly and quick eats, I hit up Big Star for tacos. My friend Christian and I just ordered from their pick up window and ate on some benches outside rather than waiting for a table. Then we hit up a few bars in Wicker Park.

Big Star Chicago | www.rtwgirl.com

Pork belly tacos at Big Star in Wicker Park

Have a beer at Estelle’s in Wicker Park

**Now open in Logan Square, check out Chicago Distilling. Haven’t been there yet as it just opened but my friends opened it up and you’ll definitely find me here when I’m in Chicago!!!

We ordered some pizza from a place called Pete’s while I was there. Doesn’t look so epic but it was delicious. In Chicago, they slice them into squares.

Pete's PIzza Chicago | www.rtwgirl.com

I like Chicago pizza because it’s not soggy. When I’m in NYC I ask pizza places to hold my slice in the oven another minute or so or well done which sounds kind of funny. Chicago has a more cooked crust and sprinkled with cornmeal. It’s awesome.

For deep dish, my go-to place is Lou Malnati’s. There are several locations throughout the city. There are other options like Uno’s, Due, Giordano’s but I love Lou’s! They have thin crust too which is awesome. For deep dish, my favorite is the spinach pie.

Mid-range to higher budget dining options:

I got to check out Chef Stephanie Izard’s (winner of Chicago Top Chef edition and James Beard Best Chef Great Lakes winner) popular restaurants Girl and The Goat and Little Goat Diner. Such great food! Big lines or hard to get reservations so planning ahead is a must!

Dinner at Girl And The Goat with friends:

Girl And The Goat Chicago | www.rtwgirl.com


Girl And The Goat Chicago | www.rtwgirl.com

An old-fashioned is a must :)

Girl And The Goat Chicago | www.rtwgirl.com

We ordered the bread. People complain because it’s not free. It’s worth it!

Girl And The Goat Chicago | www.rtwgirl.com

I always order the pork belly!

Girl And The Goat Chicago | www.rtwgirl.com

Another pork belly dish but this one was a crudo with kampachi

Girl And The Goat Chicago | www.rtwgirl.com

Diver Scallops

Little Goat is Chef Stephanie Izard’s casual eatery just down the road. We popped in for brunch one day.

Little Goat Chicago | www.rtwgirl.com

Smoked Corned Beef Hash With Poached Eggs

Little Goat Chicago | www.rtwgirl.com

Club sandwich

Little Goat Chicago | www.rtwgirl.com | www.rtwgirl.com

Goat Chili Cheese Fries

Little Goat Chicago | www.rtwgirl.com

Awesome vintage modern interior


Inside Little Goat

Due to its popularity, there is a wait here so plan accordingly!! Luckily there’s a La Colombe Coffee down the road where you can wait and have a coffee.

La Colombe Chicago | www.rtwgirl.com

Iced Coffee at La Colombe

A place I try to go for breakfast/brunch if it’s not busy is Lula Cafe. Their standard is still pretty good after all these years. It’s in the Logan Square neighborhood.

Lula Cafe Chicago | www.rtwgirl.com

Lula Cafe breakfast burrito

Lula Cafe Chicago | www.rtwgirl.com

Lula Cafe French Toast

My friend Mike took me to Longman and Eagle one afternoon. It’s a bit hipster but it was fine in the day time. It’s a hotel with a bar/restaurant and we stopped in for lunch.

Longman and Eagle Chicago | www.rtwgirl.com

Cuban sandwich at Longman & Eagle

Longman and Eagle Chicago | www.rtwgirl.com

Hamburger at Longman & Eagle

Where To Stay

The last few visits to Chicago I have stayed with friends. In the past, I always stayed in hotels. One that I can recommend is the W Lakeshore. I like the W Lakeshore’s location right by Lake Michigan but it is a trek to get around when it’s cold. So taxis or Uber are definitely needed in the winter. I do love their Bliss Spa. I could sit under their rain shower for and eat brownies all day. I’m definitely keen to try out the newer boutique properties like the James, the Langham, Public, and the Virgin Hotel. Hopefully next time!

Use this portal to book your Chicago hotel



Save this to Pinterest

Chicago: A Destination Guide | www.rtwgirl.com

What are your Chicago favorites?  Leave them in the comments!

Related Posts